Setup is SBS 2008, latest updates, with Exchange 2007 SP3. The problem is that my domain local users are getting prompted for credentials non-stop using outlook 2007.

What the credential popup asks for, is for remote.domain.com login (Welcome to mail.domain.com). It seems to be a base authentication login prompt.

I have tried many things in the exchange connection setting on the clients, trying using NTLM auth, disabling connecting over http, installed sp3 for exchange, tried enabling kernel mode authentication for the windows auth in the authentication section of each of the IIS exchange folders, i've set all the SSL settings to accept the certificates as well for each sub-site.

One thing i've noticed, is that remote.domain.com points to the local ip. Is that OK/normal ?

I got a godaddy UCC certificate installed on the SBS. The issue started to appear since i've installed that certificate. I've tried installing the certificate on the clients by right clicking the certificate and choosing install, but it didn't change much.

Really tired of messing with this one, if anyone could give an advice i'll be more than happy.

It sounds like the certificate is the problem. Do you have the FQDN of your server in the certificate in addition to the mail.domain.com and any other URLs that you have listed for your server?
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DrescaMay 25 '12 at 14:14

Hello ! Thanks. Is what my users getting really a SSL alert ? I wasn't sure, it's just asking for credentials (i know what a certificate alert is and what it looks like, but it sure doesn't look like that.. i'm getting a standard windows base auth prompt!) I 'think' i got the correct entries in my SSL certificate; server.domain.local, remote.domain.com, autodiscover.domain.com, domain.com .. it seems to have the good stuff in it ! Is it normal that the dns resolves the mail.domain.com as a local ip or that's a problem ?
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VincentMay 25 '12 at 14:50

Okay, well ran all of these commands, recycled every exchange entry in the app pool.. No go. Btw, had to change the Default Web Site for SBS Web Applications in the command since it's SBS. Do i need a server reboot or exchange services restart or anything else? thanks a lot..
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VincentMay 25 '12 at 15:03

One thing i've also noticed, is that on a new outlook profile creation, the autodiscover pops the same credentials window for mail.domain.com when it tries to do it's magic.. which i think isn't normal Even if i enter domain\user and pass and tick save, wont save. If i close outlook and reopen, it asks within 20 seconds that same credential, and then connects to exchange.. But it will then pop a little later, few minutes later.
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VincentMay 25 '12 at 15:21

Ok, this may be something with the profile's security settings. It should be set to "Negotiate Authentication" if it is set to basic I know that it will prompt you for login credentials almost every ten minutes.
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DrescaMay 25 '12 at 15:54